Many claim to be allies to marginalized groups, yet few actively engage in allyship behaviors. We focus on this disconnect and explore what barriers hinder individuals’ allyship. Open-ended responses from two representative samples of employed individuals from Michigan (n = 778) and Canada (n = 973) were analyzed. The ecological systems framework was loosely applied to map intrapersonal, interpersonal, and contextual barriers to allyship from the perspectives of potential allies in their workplaces. Results were consistent across the two samples and revealed that about 19% of barriers arose from the organizational context (e.g., lack of training), and 8% arose from interpersonal dynamics (e.g., lack of coworker support). Among intrapersonal barriers, cognitive (9.5%) and motivational (9.5%) factors rose to the top; fewer responses pertained to personality (5%), social identity (5%), or emotional barriers (2%); 27.5% claimed no barriers. Given the predominance of the organizational context and workplace interpersonal barriers, as well as leaders’ ability to influence individuals’ cognitive and motivational (intrapersonal) barriers, this paper highlights the need for organizations to adopt a systems perspective. Organizations can play a stronger role in empowering and nurturing employees’ allyship and provide low-risk, structured opportunities for allyship action that simultaneously builds trusting relationships among coworkers.